Direct synthesis of pyrroles from imines, alkynes, and acid chlorides: An isocyanide-mediated reaction

Organic Letters

Volumn 9, Issue 3, 2007, Pages 449-452

  St Cyr, Daniel J ^a   Martin, Nicolas ^a   Arndtsen, Bruce A ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CHLORIDE; CYANIDE; IMINE; PALLADIUM; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; SYNTHESIS;

ALKYNES; CATALYSIS; CHLORIDES; CYANIDES; IMINES; MODELS, CHEMICAL; PALLADIUM; PYRROLES;

EID: 33847080427     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062773j     Document Type: Article

References (45)

1. Representative examples: (a) Thompson, R. B. FASEB J. 2001, 15, 1671.
2. (b) Muchowski, J. M. Adv. Med. Chem. 1992, 1, 109.
3. Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305. For reviews:
4. Rossi, R.; Bellina, F. Tetrahedron 2006, 62, 7213.
5. (e) Walsh, C. T.; Garneau-Tsodikova, S.; Howard-Jones, A. Nat. Prod. Rep. 2006, 23, 517.
6. (f) Gribble, G. W. In Comprehensive Heterocydic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Oxford, UK, 1996; Vol. 2, p 207.
7. (g) Jones, R. A. Pyrroles, Part II; Wiley: New York, 1992.
8. (h) Le Quesne, P. W.; Dong, Y.; Blythe, T. A. In Alkaloids: Chemical and Biological Perspectives; Pelletier S. W., Ed.; Pergamon: Elmsford, NY, 1999; Vol. 13, p 238.
9. (a) Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds. Handbook of Conducting Polymers, 2nd ed.; Marcel Dekker: New York, 1998.
10. (b) Ramanavicius, A.; Ramanaviciene, A.; Malinauskas, A. Electrochem. Acta 2006, 51, 6025.
11. Novak, P.; Müller, K.; Santhanam, K. S. V.; Haas, O. Chem. Rev. 1997, 97, 207.
12. For example: Boger, D. L.; Boyce, C. W.; Labrilli, M. A.; Sehon, C. A.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 54.
13. Knorr, L. Chem. Ber 1884, 17, 1635.
14. Paal, C. Chem. Ber. 1885, 18, 367.
15. Hantzsch, A. Ber. Dtsch. Chem. Ges. 1890, 23, 1474.
16. Recent examples: (a) Balme, G. Angew. Chem., Int. Ed. 2004, 43, 6238.
17. (b) Nair, V.; Vinod, A. U.; Rajesh, C. J. Org. Chem. 2001, 66, 4427.
18. Bharadwaj, A. R; Scheldt, K. A. Org. Lett. 2004, 6, 2465.
19. Tejedor, D.; Gonzalez-Cruz, D.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Rodriguez, M. L. J. Am. Chem. Soc. 2004, 126, 8390.
20. (e) Ranu, B. C.; Dey, S. S. Tetraherdron Lett. 2003, 44, 2865.
21. (f) Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T. Heterocydes 1999, 50, 463.
22. Recent examples: (a) Braun, R. U.; Zietler, K.; Müller, T. J. J. Org. Lett. 2001, 3, 3297.
23. (b) Nishibayashi, Y.; Yoshikawa, M.; Inada, Y.; Milton, M. D.; Hidai, M.; Uemura, S. Angew. Chem., Int. Ed. 2003, 42, 2681.
24. Shiraishi, H.; Nishitani, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 6234.
25. Gorin, D. J.; Davis, N. R.; Toste, D. F. J. Am. Chem. Soc. 2005, 127, 11260.
26. (e) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074.
27. (f) Declerk, V.; Ribiere, P.; Martinez, J.; Lamaty, F. J. Org. Chem. 2004, 69, 8372.
28. (g) Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9260.
29. (h) Larionov, O. V.; de Meijere, A. Angew. Chem., Int. Ed. 2005, 44, 5664.
30. (a) Dhawan, R.; Arndtsen, B. A. J. Am. Chem. Soc. 2004, 126, 468.
31. (b) Dhawan, R.; Dghaym, R. D.; Arndtsen, B. A. J. Am. Chem. Soc. 2003, 125, 1474.
32. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
33. (a) Ugi, I. Angew. Chem., Int. Ed. 1962, 1, 8.
34. (b) Diaz, J. L.; Miguel, M.; Lavilla, R. J. Org. Chem. 2004, 69, 3550.
35. For related [4 + 1] cycloadditions: (a) Morel, G.; Marchand, E.; Benjelloun, A. T.; Sinbandhit, S.; Guillou, O.; Gall, P. Eur. J. Org. Chem., 1998, 11, 2631.
36. (b) Marchand, E.; Morel, G. Tetrahedron Lett. 1993, 34, 2319.
37. Berthet, J.-C.; Nierlich, M.; Ephritikhine, M. Eur. J. Org. Chem. 2002, 2, 375.
38. Deyrup, J. A.; Killion, K. K. J. Heterocycl. Chem. 1972, 9, 1045.
39. (a) Berree, F.; Morel, G. Tetrahedron 1995, 51, 7019.
40. (b) Berree, F.; Malvaut, Y.; Marchand, E.; Morel, G. J. Org. Chem. 1993, 58, 6022.
41. (a) Gribble, G. W. Oxazoles: Synthesis, Reactions, and Spectroscopy, Part A; Palmer, D. C., Ed.; Wiley: New York, 2003; Vol. 60, Chapter 4, p 473.
42. (b) Gribble, G. W. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., William, W. H., Eds.; Wiley: New York, 2002; Vol. 59, Chapter 10, p 681.
43. McEwen, W. E.; Kanitkar, K. B.; Hung, W. M. W. J. Am. Chem. Soc. 1971, 93, 4484.
44. Enolizable iminium salts readily form enamides, which do not provide pyrroles under palladium catalysis (ref 9).
45. Bailly, C. Curr. Med. Chem.: Anti-Cancer Agents 2004, 4, 363.